Lt. Col Lipson graduated from Villanova University in 1992.   After being commissioned as a Second Lieutenant, he reported to the Basic School and later to Communications Officer School in Quantico.

 In January of 1994, LtCol Lipson was assigned to headquarters II Marine Expeditionary Force, Camp Lejeune, as the Information Systems Management Officer, G6. While at Camp Lejeune, LtCol Lipson deployed with the 22nd Marine Expeditionary Unit (Special Operations Capable) as the S6a participating in Operation Joint Endeavor in Bosnia and Herzegovina as well as Operation Assured Response in Liberia. LtCol Lipson finished his tour in Camp Lejeune as the Special Projects Officer for the G6, 2nd Fleet Service Support Group.

 In February of 1997, LtCol Lipson joined the Select Marine Corps Reserve as the Targeting Officer with Marine Air Group-49. In July 1998 LtCol Lipson attended the Naval Marine Intelligence Training Center for MOS training. In January of 1999, LtCol Lipson became the S2 for HQ Battery, 3/14.  LtCol Lipson joined the Marine Corps Intelligence Agency in October of 2001, serving as a Middle East Analyst, assisting with Operation Enduring Freedom in Afghanistan.  In March of 2003, LtCol Lipson returned to MAG-49 as the S2.

 In July 2004, LtCol Lipson was activated in support of Operation Iraqi Freedom and was assigned to the 4th Civil Affairs Group as the S6. He also was a Civil Affairs Team Leader.

 After returning home from Fallujah in May 2005, LtCol Lipson resumed his duties as the S2 at MAG-49. LtCol Lipson became the Executive Officer in October 2008 until June 2010.

In January 2011, LtCol Lipson was mobilized to join Marine Forces Cyber Command as the CentCom Regional Team Lead, providing full spectrum cyber support to overseas contingency operations.